(E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester | 503446-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester
• CAS: 503446-45-5
• 化学式: C₃₅H₅₀O₅
• 分子量: 550.779
• InChiKey: FCUJNDJOLDJENY-FVQCZDFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic studies on the dienophile unit of methyl isosartortuoate. Part 2: SmI2-mediated 14-membered carbocyclization

  摘要：

  The dienophile unit of methyl isosartortuoate has been synthesized. The 14-membered carbocycle was constructed by a SmI2-mediated intramolecular Reformatsky reaction. The introduction of the oxo group at the gamma-position of the alpha,beta-unsaturated ester was achieved by rearrangement of an beta,gamma-epoxy ester. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02603-5
• 作为产物：
  描述：

  (E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester 在 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 (E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-3-hydroxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic studies on the dienophile unit of methyl isosartortuoate. Part 2: SmI2-mediated 14-membered carbocyclization

  摘要：

  The dienophile unit of methyl isosartortuoate has been synthesized. The 14-membered carbocycle was constructed by a SmI2-mediated intramolecular Reformatsky reaction. The introduction of the oxo group at the gamma-position of the alpha,beta-unsaturated ester was achieved by rearrangement of an beta,gamma-epoxy ester. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02603-5